Adduct of cyclo-butane-1, 2-dicyanide with sulfuric acid monohydrate and method of making same



United States Patent ADDUCT 61F CYCLU EUTANE 1,2 DKCYANEDE WITH SULFUREC AGED MUNOHYDRATE AND METHGD 6F MAKENG SAME Janice lL. Greene, Warrensville Heights, and James D.

idol, in, Shaker Heights, Ohio, assignors to The Standgrgl @il Company, Cleveland, @hio, a corporation or it) No Drawing. Filed Aug. 3, 1962, Ser. No. 214,532 2 Claims. (Cl. 260-464) This invention relates to the cyclo-butane-1,2-di cyanide adduct with sulfuric acid monohydrate. The invention is also concerned with the method of making the adduct by reacting cyclo-butane-1,2-dicyanide with the monohydrate of sulfuric acid.

Either the cis or trans forms of the cyclo-butane-l,2-dicyanide can be used as a starting material to form cis or trans dicarboxamide adducts. The invention is also applicable to a mixture. The trans-cyclo-butane-1,2-dicyanide is the more readily available starting material and this form will be described in the preferred embodiment hereinafter.

The starting materials and relative amounts are indicated by the following formulas:

The exact molecular configuration of the product has not been established but it has the following general formula:

o-o-oz where Z has the empirical formula:

I-I O NS The structure is postulated to be ture, the shorter the reaction time, and the lower the temperature, the longer the reaction time. The reaction is exothermic and external cooling can be used if desired. Temperatures of from 50 to 95 C. are preferred because higher temperatures may somewhat aitect the stability of the cycle-butane ring. The preferred reaction time in this temperature range is 1 to 2 hours.

The relative amounts of the reaction components are preferably theoretical, but an excess of either can be used in the process, but will remain in the final product unless steps are taken to separate it.

The adduct made in accordance with the present invention is useful as a chemical intermediate, such as in the formation of cyclobutanc-l,2dicarboxamide, the preparation of which is described in our copending application Serial No. 214,531, now Patent No. 3,110,729 filed of even date herewith, the disclosure of which is incorporated by reference.

T he-following is the best mode contemplated for carrying out the invention:

Example I Theoretical, Actual,

percent percent Carbon 21. 3 20. 99 Hydrogen 4. 4. 07 Nitrogen 8. 7. 96 Sulfur 18. 95 18.75

In addition to the above analysis, the nuclear magnetic resonance spectrum confirms the presence of the cyclobutane ring and the infrared spectrum confirms the absence of any nitrile groups. Products made from the adduct have the 1,2-configuration confirming the 1,2-positions of Z in the adduct.

We claim:

1. The method of preparing an adduct, which comprises the step of reacting 1 mole of cyclo-butane-1,2-dicyanide with 2 moles of the monohydrate of sulphuric acid, said reaction being continued for from 15 minutes to four hours at a temperature of to 125 0., followed by cooling to ambient temperature, and recovering the adduct.

2. The method of preparing an adduct, which comprises i the step of adding cyclo-butane-1,2-dicyanide to the monohydrate of sulfuric acid in the ratio of 1 mol of the dicyanide to 2 mols of the monohydrate, While maintaining a temperature of to C., followed by cooling to ambient temperature, and recovering the adduct.

No references cited.

CHARLES B. PARKER, Primary Examiner. 

1. THE METHOD OF PREPARING AN ADDUCT, WHICH COMPRISES THE STEP OF REACTING 1 MOLE OF CYCLO-BUTANE-1,2-DICYANIDE WITH 2 MOLES OF THE MONOHYDRATE OF SULPHURIC ACID, SAID REACTION BEING CONTAINUED FOR FROM 15 MINUTES TO FOUR HOURS AT A TEMPERATURE OF 40 TO 125*C., FOLLOWED BY COOLING TO AMBIENT TEMPERATURE, AND RECOVERING THE ADDUCT. 